ReactIR Inline FTIR Implementation applications, communications, environment and sampling
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1 ReactIR Inline FTIR Implementation applications, communications, environment and sampling Dr. Florian Eigenmann Head of Reaction Analysis with IR Milano, October
2 Agenda scale up: from lab to plant Technology FTIR Online ATR with AgX fibers vs. atline ATR (lab) - Sampling - Temperature, pressure high pressure adapter - Monitoring trends, capturing intermediates, end point determination with e.g. rate of change monitoring Implementation in process applications - Bypass, ProSys - ShuF valve - Dip Tube ic Process workflow
3 Near, mid and far infrared Infrared Region Energy Near-IR (12, cm -1 ) - Combination & Overtones of Fundamental Vibrations - Broad Features (poor Qual) - Lower ε (good Quant) - O-H, N-H, S-H, C-H Mid-IR ( cm -1 ) - Fundamental Vibrations - Sharp Features (good Qual) - High ε (good Quant) - Most organic functional groups Far-IR ( cm -1 ) - Fundamental Vibrations - Sharp Features (good Qual) - Lattice, Inorganics, Heavy Atoms
4 Infrared Spectroscopy Interaction of light and material In the infrared range: Excitation of molecular vibrations
5 The infrared (IR) spectrum of water Transmission 0% 50% 100% wavenumber cm
6 Infrared Spectroscopy Transmission 0% 50% 100% Qualitative Analysis -Like a fingerprint: Each molecule has its own individual IR spectrum wavenumber cm
7 Infrared Spectroscopy Transmission 0% 50% 100% Quantitative Analysis -Lambert and Beer s law: A is ~ c 2500 wavenumber cm
8 Functional Groups 7
9 Background of ReactIR 1.5 Intensity Wavenumber (cm-1) 8
10 With Single Beam 9
11 Absorbance spectrum Reference Spectra Wavenumber (cm-1) 10
12 Silicon probe: cm -1 isocyanate (~2275 cm-1) acetylene (~2200 cm-1) isothiocyanate cyanide, cyanate ( cm-1) C=N (~2150 cm-1) azide (~2100 cm-1) silane (~2050 cm-1) BH 3 (~2100 cm-1) ketene (~2200 cm-1) allene (~1975 cm-1)
13 Absorbance of IR light Source Sample Detector Intensity Wavenumber
14 ReactIR Method of Measurement Attenuated Total Reflectance (ATR) sensor in the probe tip Why ATR for in situ monitoring applications? - Pathlength = (depth of penetration) x number of reflections = 16 μm - No interference from bubbles, solid, mixing, etc. - Selective information on the liquid phase - Beer s Law: A=abc - a & b are constants so A is proportional to concentration! a absorptivity, extinction coefficient b optical pathlength into the sample (cm) c solute molar concentration (mol/l) Depth of Penetration (DP) is approximately 2μm Number of Reflections is approximately 8 (for fiber probes)
15 IR Spectrum of Ethyl Acetate C-C-O C=O OCH 2 CH 3 -C=O
16 ReactIR Reference Spectra Reference Spectra THF 1066cm cm -1 Toluol Water 907cm cm -1 ReactIR observes distinct peaks for each component :00PM 10mL room temperature magnetic stirring
17 ReactIR 45P Plant Trial Study of THF/Water/Toluene Collected reference spectra of THF, toluene and water Started ProSys setup with only THF (100kg) at room temperature Added 1kg water and waited for equilibrium repeated for two additional 1kg water addition Added 1kg toluene and waited for equilibrium repeated for toluoene additions of 1.75kg ReactIR spectrum collected every 30secs Paused experiment and moved instrument to measurement cart Resumed data collection to check for vibration issues Added another 2.25kg of toluene 16
18 Real-Time Water in THF Monitoring First Water Addition THF Peak at 907cm -1 Water Peak at 1640cm -1 Rate of Change (1st Deriv) of Water peak at 1640cm -1 Added 1kg of water Off-line CHP ~850 ReactIR45P tracks the water addition and gives insight 15:00PM into 10mL room temperature magnetic stirring ProSys retention time 17
19 Real-Time Water in THF Monitoring Second Water Addition Water Peak at 1640cm -1 THF Peak at 907cm -1 Rate of Change (1st Deriv) of Water peak at 1640cm -1 Off-line CHP ~850 ReactIR45P tracks the water additions and shows 15:00PM excellent 10mL room temperature magnetic stirring data repeatability 18
20 Real-Time Water in THF Monitoring Third Water Addition THF Peak at 907cm -1 Water Peak at 1640cm -1 Rate of Change (1st Deriv) of Water peak at 1640cm -1 ReactIR45P tracks the water additions and again 15:00PM shows 10mL room temperature magnetic stirring excellent data repeatability 19
21 Real-Time Toluol in THF/Water Monitoring Toluene Additions Toluene Peak at 733cm -1 Rate of Change (1st Deriv) of Toluol peak at 733cm -1 ReactIR45P tracks the toluol additions and again 15:00PM shows 10mL room temperature magnetic stirring excellent data repeatability 20
22 Final Conclusions ReactIR has high potential to better understand new product reactions and increase productivity by more quickly optimizing processes With the data provided by ReactIR, real-time information can be gained - Determine reaction end point - Provide specific information on reaction progression - possible reactive intermediates? which cannot be captured by standard on-line techniques - Immediately know if a reagent is accumulating or if a reaction has stalled ReactIR is a highly sensitive, reaction analysis system which can detect growing of isolated peaks in the regions of interest under low concentration conditions calibration free Inherent safety plus better reaction understanding and faster process optimization
23 Diisocynate reaction to form a prepolymer 22
24 Surface Plot (3D or waterfall plot) 23
25 Comparison with off-line sampling 24
26 White papers about NCO and Borohydride 25
27 Sampling Options in Large Scale Reactors
28 AgX Technology 6 th Generation Optimized Tip - Complete re-design of tip (6.3mm & 9.5mm OD/ Larger aspect ratio) - Lower potential for fouling - Smaller diameter sheathing greater flexibility Detect lower concentration reaction components - 25% performance & SNR increase - 8 reflection, flat ATR sensor (previous DS design only 6 reflections)
29 High pressure adaptor 28 Confidential Internal Use Only
30 High pressure adaptor 29 Confidential Internal Use Only
31 Bypass sampling: ProSys 30 Confidential Internal Use Only
32 Implementations fouling challenges The flow of the mixture was anticlockwise. The position of the Diamond window of the probe seems not to be ideal. One problem could be that the flow goes against the probe and some material accumulate inside the windows. The best flow would be from the side of the window. In this way the diamond gets cleaned with the flow automatically. Confidential Internal Use Only
33 The solution: Retractable Probe Accessory Kit This direct-insertion accessory enables easy disconnection from chemistry and reduces the need for probe re-alignment Confidential Internal Use Only
34 The solution: Retractable Probe Accessory Kit Confidential Internal Use Only
35 Sampling Options in Large Scale Reactors
36 Novel PAT interface Access all areas In September of 2010, May Ling Yeow from Pfizer UK and her colleagues published an article on tcetoday.com (tce REACTOR DESIGN) detailing their extensive use of the MonARC FTIR system in combination with the ShuF-Feterolf disc valve. We will explore the benefits of using the ShuF Feterolf valve in greater detail, but it is useful to add a few excerpts from this interesting article. 35 Confidential Internal Use Only
37 Access all areas Drain valve interface FTIR probe (blue) and RTD (red) contact process liquid here. FTIR probe and RTD enter disc valve assembly here. 36 Confidential Internal Use Only
38 Access all areas Process improvement The region of the spectrum used to generate a peak area calculation is shown on the top right. The trend of the reaction s starting material is shown on the bottom right. It can be seen that the reaction progress is trended and an accurate endpoint can be determined in real-time without removing material from the reactor for analysis 37 Confidential Internal Use Only
39 Drain valve interface IFPAC 2015, Arlington VA, Christian Lautz (Roche) 38 Confidential Internal Use Only
40 Drain valve interface IFPAC 2015, Arlington VA, Christian Lautz (Roche) 39 Confidential Internal Use Only
41 Drain valve interface IFPAC 2015, Arlington VA, Christian Lautz (Roche) 40 Confidential Internal Use Only
42 Drain valve interface connection with f.o. IFPAC 2015, Arlington VA, Christian Lautz (Roche) 41 Confidential Internal Use Only
43 Sampling Options in Large Scale Reactors
44 Dip Tube Adaptation Temperature up to 180 C MT Dip Tube Adapter
45 Standard Conduit specifications 50 C - No change in conduit 80 C - Slight color change and conduit is more flexible - Rubber sheathing is a little tacky and more playable. 100 C - noticeably more flexible and tacky - feels like the sheathing could slide against the inner metal core with a lot of pressure but I could not make it but it just feels like it could potentially slide with enough force 125 C - Fiber nose piece can pull away from sheathing, sheathing slides along metal core with force 150 C - Fiber nose piece easily pulls off of sheathing with a little force 180 C - Smoking and sheathing is coming off of metal core with no force. 44
46 Dip Tube Adaptation: robust conduit 45
47 Temperature stable conduit Length: 4.00 m Temperature: 180 C 46
48 Brief Review of the icir Workflow
49 configuration Page 48 Confidential Internal Use Only
50 ic Process Method Selection Choose a method before beginning ReactIR 45P ReactIR 45P ReactIR 45P 49 Confidential Internal Use Only
51 Brief Introduction to the ic Process Workflow Expert user creates a template in ic IR (includes trends, peaks, data treatments, ic Quant) Expert user can use ic IR to further analyze any data collected by operator Administrator can import ic IR template into ic Process as a method and add external outputs (DCS) and alarms then approve method. Operator can select from approved methods, start/stop instrument, start/stop batches, and collect backgrounds ic Process archives collected data into the archive folder as ic IR files and also keeps a copy of the last 10 days of data
52 ReactIR Solutions: From Research to Manufacturing Quick & easy Full range of applications Scale-up and Manufacturing ReactIR TM 15 & FlowIR ReactIR TM 45m ReactIR TM 45P Ease of use ReactIR 15 Integrated Temp DS only Mulitplex ( 2 sampling points) Full application range (Pressure, temp, flow) 51 Hydrogenations lab to plant Pilot /Plant batches ATEX
53 Addressing Today s Challenges Software Data capture enables institutional knowledge sharing and building Probes and Analytics More information per experiment for increased understanding of chemistry and processes 52 Reactor Platforms Increased personal productivity delivers more successful experiments per researcher Confidential Internal Use Only
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59 58 Confidential Internal Use Only
60 America's Cup 2007 Page 59 Confidential Internal Use Only
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